{"id":"https://openalex.org/W2123757481","doi":"https://doi.org/10.1021/ol401636d","title":"Synthesis of trans-2-(Trifluoromethyl)cyclopropanes via Suzuki Reactions with an N-Methyliminodiacetic Acid Boronate","display_name":"Synthesis of trans-2-(Trifluoromethyl)cyclopropanes via Suzuki Reactions with an N-Methyliminodiacetic Acid Boronate","publication_year":2013,"publication_date":"2013-08-16","ids":{"openalex":"https://openalex.org/W2123757481","doi":"https://doi.org/10.1021/ol401636d","mag":"2123757481","pmid":"https://pubmed.ncbi.nlm.nih.gov/23952128"},"language":"en","primary_location":{"id":"doi:10.1021/ol401636d","doi":"https://doi.org/10.1021/ol401636d","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ol401636d","pdf_url":null,"source":{"id":"https://openalex.org/S201989124","display_name":"Organic Letters","issn_l":"1523-7052","issn":["1523-7052","1523-7060"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic Letters","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref","pubmed"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5041051375","display_name":"Matthew A. J. Duncton","orcid":"https://orcid.org/0000-0002-6007-7515","observed_orcids":["https://orcid.org/0000-0002-6007-7515"]},"institutions":[{"id":"https://openalex.org/I4210159901","display_name":"Rigel (United States)","ror":"https://ror.org/05j0yvv31","country_code":"US","type":"company","lineage":["https://openalex.org/I4210159901"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Matthew A. J. Duncton","raw_affiliation_strings":["Rigel, Inc., 1180 Veterans Boulevard, South San Francisco, California 94080, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Rigel, Inc., 1180 Veterans Boulevard, South San Francisco, California 94080, United States","institution_ids":["https://openalex.org/I4210159901"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5101698188","display_name":"Rajinder Singh","orcid":"https://orcid.org/0000-0002-6174-4973","observed_orcids":["https://orcid.org/0000-0002-6174-4973"]},"institutions":[{"id":"https://openalex.org/I4210159901","display_name":"Rigel (United States)","ror":"https://ror.org/05j0yvv31","country_code":"US","type":"company","lineage":["https://openalex.org/I4210159901"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Rajinder Singh","raw_affiliation_strings":["Rigel, Inc., 1180 Veterans Boulevard, South San Francisco, California 94080, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Rigel, Inc., 1180 Veterans Boulevard, South San Francisco, California 94080, United States","institution_ids":["https://openalex.org/I4210159901"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5041051375"],"corresponding_institution_ids":["https://openalex.org/I4210159901"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":2.9185,"has_fulltext":false,"cited_by_count":65,"citation_normalized_percentile":{"value":0.91086793,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":93,"max":99},"biblio":{"volume":"15","issue":"17","first_page":"4284","last_page":"4287"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11611","display_name":"Cyclopropane Reaction Mechanisms","score":0.8705999851226807,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T11611","display_name":"Cyclopropane Reaction Mechanisms","score":0.8705999851226807,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T10947","display_name":"Fluorine in Organic Chemistry","score":0.0860000029206276,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T11441","display_name":"Organoboron and organosilicon chemistry","score":0.016699999570846558,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/suzuki-miyaura-coupling","display_name":"Suzuki coupling","score":0.7400000095367432},{"id":"https://openalex.org/keywords/cyclopropanation","display_name":"cyclopropanation","score":0.6460000276565552},{"id":"https://openalex.org/keywords/vinylboronic-acids","display_name":"vinylboronic acids","score":0.8190000057220459},{"id":"https://openalex.org/keywords/trans-stereochemistry","display_name":"trans stereochemistry","score":0.734000027179718},{"id":"https://openalex.org/keywords/boronic-acid-synthesis","display_name":"boronic acid synthesis","score":0.44200000166893005}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9471133947372437},{"id":"https://openalex.org/C2776442012","wikidata":"https://www.wikidata.org/wiki/Q2302144","display_name":"Trifluoromethyl","level":3,"score":0.9437016248703003},{"id":"https://openalex.org/C2780374730","wikidata":"https://www.wikidata.org/wiki/Q413683","display_name":"Diazomethane","level":2,"score":0.9016779661178589},{"id":"https://openalex.org/C138716334","wikidata":"https://www.wikidata.org/wiki/Q268477","display_name":"Diastereomer","level":2,"score":0.7751774787902832},{"id":"https://openalex.org/C2781076698","wikidata":"https://www.wikidata.org/wiki/Q718074","display_name":"Aryl","level":3,"score":0.6438086032867432},{"id":"https://openalex.org/C13205572","wikidata":"https://www.wikidata.org/wiki/Q899891","display_name":"Suzuki reaction","level":4,"score":0.5776086449623108},{"id":"https://openalex.org/C2780378348","wikidata":"https://www.wikidata.org/wiki/Q25351438","display_name":"Ring (chemistry)","level":2,"score":0.5412108898162842},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.45787331461906433},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.4121844470500946},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.35054296255111694},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.0}],"mesh":[{"descriptor_ui":"D001897","descriptor_name":"Boronic Acids","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D001897","descriptor_name":"Boronic Acids","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D002384","descriptor_name":"Catalysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D003521","descriptor_name":"Cyclopropanes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D003521","descriptor_name":"Cyclopropanes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D004952","descriptor_name":"Esters","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D006845","descriptor_name":"Hydrocarbons, Fluorinated","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D006845","descriptor_name":"Hydrocarbons, Fluorinated","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D007098","descriptor_name":"Imino Acids","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D010165","descriptor_name":"Palladium","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D013237","descriptor_name":"Stereoisomerism","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D020650","descriptor_name":"Combinatorial Chemistry Techniques","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/ol401636d","doi":"https://doi.org/10.1021/ol401636d","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ol401636d","pdf_url":null,"source":{"id":"https://openalex.org/S201989124","display_name":"Organic Letters","issn_l":"1523-7052","issn":["1523-7052","1523-7060"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic Letters","raw_type":"journal-article"},{"id":"pmid:23952128","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/23952128","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic letters","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":36,"referenced_works":["https://openalex.org/W52618550","https://openalex.org/W92405287","https://openalex.org/W1972084879","https://openalex.org/W1975252703","https://openalex.org/W1987640473","https://openalex.org/W1996100382","https://openalex.org/W1999135579","https://openalex.org/W2007029901","https://openalex.org/W2013422701","https://openalex.org/W2036121419","https://openalex.org/W2036699925","https://openalex.org/W2047738597","https://openalex.org/W2060531713","https://openalex.org/W2061395384","https://openalex.org/W2074274985","https://openalex.org/W2075671408","https://openalex.org/W2083254051","https://openalex.org/W2085366031","https://openalex.org/W2096095251","https://openalex.org/W2096885367","https://openalex.org/W2102543514","https://openalex.org/W2103458395","https://openalex.org/W2105361411","https://openalex.org/W2106033527","https://openalex.org/W2110408266","https://openalex.org/W2111115182","https://openalex.org/W2116087305","https://openalex.org/W2126220849","https://openalex.org/W2147111608","https://openalex.org/W2153810710","https://openalex.org/W2155597099","https://openalex.org/W2160524374","https://openalex.org/W2165292195","https://openalex.org/W2326304147","https://openalex.org/W2326508858","https://openalex.org/W4243023822"],"related_works":["https://openalex.org/W2950837307","https://openalex.org/W2174839415","https://openalex.org/W2090146613","https://openalex.org/W2106033527","https://openalex.org/W2950100931","https://openalex.org/W2052415032","https://openalex.org/W2952275585","https://openalex.org/W3111919308","https://openalex.org/W2063947615","https://openalex.org/W2153979029"],"abstract_inverted_index":{"trans-2-(Trifluoromethyl)cyclopropylboronic":[0],"acid":[1,3,15],"N-methyliminodiacetic":[2],"(MIDA)":[4],"ester":[5,17],"5":[6,36],"was":[7],"synthesized":[8],"as":[9],"a":[10,21,41],"pure":[11],"diastereomer":[12],"from":[13],"vinylboronic":[14],"MIDA":[16],"and":[18],"(trifluoromethyl)diazomethane":[19],"in":[20,37,52],"single":[22],"step.":[23],"An":[24],"X-ray":[25],"study":[26],"confirmed":[27],"the":[28,31],"trans-stereochemistry":[29],"around":[30],"cyclopropyl":[32],"ring.":[33],"Use":[34],"of":[35,43],"Suzuki":[38],"reactions,":[39],"with":[40],"variety":[42],"aryl":[44],"or":[45],"heteroaryl":[46],"coupling":[47],"partners,":[48],"provided":[49],"trans-2-(trifluoromethyl)cyclopropyl":[50],"products":[51],"moderate":[53],"to":[54],"excellent":[55],"yields":[56],"(17-90%).":[57]},"counts_by_year":[{"year":2026,"cited_by_count":4},{"year":2025,"cited_by_count":2},{"year":2024,"cited_by_count":2},{"year":2023,"cited_by_count":5},{"year":2022,"cited_by_count":5},{"year":2021,"cited_by_count":3},{"year":2020,"cited_by_count":9},{"year":2019,"cited_by_count":5},{"year":2018,"cited_by_count":4},{"year":2017,"cited_by_count":5},{"year":2016,"cited_by_count":7},{"year":2015,"cited_by_count":7},{"year":2014,"cited_by_count":7}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}